Condensed-cyclic compound and organic light emitting diode including the same

ABSTRACT

Embodiments of the present invention are directed to a condensed-cyclic compound and an OLED including the same.

CROSS-REFERENCE TO RELATED PATENT APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2011-0143911, filed on Dec. 27, 2011 in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND

1. Technical Field

The present invention relates to a condensed-cyclic compound and anorganic light-emitting diode including the same.

2. Description of the Related Art

Organic light-emitting diodes (OLEDs) are self-emitting devices havingadvantages such as wide viewing angles, good contrast, quick responsetimes, high brightness, and good driving voltage. OLEDs can providemulticolored images. A typical OLED has a structure including asubstrate, and an anode, a hole transport layer (HTL), an emission layer(EML), an electron transport layer (ETL), and a cathode sequentiallystacked on the substrate. In this regard, the HTL, the EML, and the ETLare organic layers formed of organic compounds.

An operating principle of an OLED having the above-described structureis as follows.

When a voltage is applied between the anode and the cathode, holesinjected from the anode move to the EML via the HTL, and electronsinjected from the cathode move to the EML via the ETL. The holes andelectrons recombine in the EML to generate excitons. When the excitonsdrop from an excited state to a ground state, light is emitted.

SUMMARY

According to an aspect of the present invention, there is provided acondensed-cyclic compound represented by Formula 1 below:Ar₁

Ar₂)_(q)  Formula 1

In Formula 1, Ar₁ may be a substituted or unsubstituted C₅-C₆₀ aromaticring or a substituted or unsubstituted C₂-C₆₀ heteroaromatic ring.

q may be an integer of 1 to 6, and when q is 2 or greater, the 2 or moreof the Ar₂ groups may be identical to or different from each other.

In some embodiments, Ar₂ may be represented by Formula 2 below:

In Formula 2, Cy may be a substituted or unsubstituted C₃ to C₈cycloalkane.

X₁ may be N(R₁₁), B(R₁₁), Si(R₁₁)(R₁₂), O, or S.

X₂ may be a single bond or —[C(R₁₅)(R₁₆)]_(n)—, where n is an integer of1 to 3, but when n is 2 or greater, the 2 or more R₁₅ and R₁₆ groups maybe identical to or different from each other.

L₁ may be a single bond, a substituted or unsubstituted C₁-C₆₀ alkylenegroup, a substituted or unsubstituted C₂-C₆₀ alkenylene group, asubstituted or unsubstituted C₂-C₆₀ alkynylene group, a substituted orunsubstituted C₃-C₆₀ cycloalkylene group, a substituted or unsubstitutedC₂-C₆₀ heterocycloalkylene group, a substituted or unsubstituted C₅-C₆₀arylene group, or a substituted or unsubstituted C₂-C₆₀ heteroarylene.

R₁ through R₃, R₁₁, R₁₂, R₁₅, and R₁₆ may each independently behydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₁₀-C₆₀ alkylthio group, a substituted or unsubstitutedC₃-C₆₀ cycloalkyl group, a substituted or unsubstituted C₅-C₆₀ arylgroup, a substituted or unsubstituted C₅-C₆₀ aryloxy group, asubstituted or unsubstituted C₅-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a (substituted or unsubstitutedC₁-C₆₀ alkyl)amino group, a di(substituted or unsubstituted C₁-C₆₀alkyl)amino group, or a (substituted or unsubstituted C₅-C₆₀ aryl)aminogroup, or a di(substituted or unsubstituted C₅-C₆₀ aryl) amino group.

a may be an integer of 1 to 3, and when a is 2 or greater, the 2 or moreR₃ groups may be identical to or different from each other.

* may be a binding site to Ar₁ of Formula 1.

According to another aspect of the present invention, there is providedan organic light-emitting diode including a first electrode; a secondelectrode facing the first electrode; and an organic layer between thefirst electrode and the second electrode, wherein the organic layer mayinclude at least one of the condensed-cyclic compounds.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other features and advantages of the present inventionwill become more apparent by reference to the following detaileddescription when considered in conjunction with the attached drawings inwhich:

FIG. 1 is a schematic diagram illustrating an organic light-emittingdiode (OLED) according to an embodiment of the present invention;

FIG. 2 is a thermogravimetric analysis (TGA) graph of Compound 38;

FIG. 3 is a TGA graph of Compound 262;

FIG. 4 is a TGA graph of Compound 586;

FIG. 5 is a TGA graph of Compound 726;

FIG. 6 is a TGA graph of Compound 929;

FIG. 7 is a voltage-current density graph of the OLEDs of Examples 1through 5 and Comparative Examples 1 through 3;

FIG. 8 is a voltage-efficiency graph of the OLEDs of Examples 1 through5 and Comparative Examples 1 through 3; and

FIG. 9 is a photoluminescence (PL) spectrum of the OLEDs of Examples 1through 5 and Comparative Examples 1 through 3.

DETAILED DESCRIPTION

Hereinafter, the present embodiments will be described more fully withreference to the accompanying drawings, in which exemplary embodimentsare shown. As used herein, the term “and/or” includes any and allcombinations of one or more of the associated listed items. Expressionssuch as “at least one of,” when preceding a list of elements, modify theentire list of elements and do not modify the individual elements of thelist.

According to an embodiment of the present invention, there is provided acondensed-cyclic compound represented by Formula 1 below:Ar₁

Ar₂)_(q)  Formula 1In Formula 1, Ar₁ may be a substituted or unsubstituted C₅ to C₆₀aromatic ring or a substituted or unsubstituted C₂ to C₆₀ heteroaromaticring, and q is an integer of 1 to 6. When q is 2 or greater, the 2 ormore Ar₂ groups may be identical to or different from each other. Ar₂ isrepresented by Formula 2 below:

For example, Ar₁ of Formula 1 may be represented by any one of Formulae3A through 3G below:

In Formulae 3A through 3G, R₂₀ through R₃₉ are each independently abinding site to Ar₂ (represented by Formula 2), hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxylic acid groupor a salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₁-C₆₀alkylthio group, a substituted or unsubstituted C₃-C₆₀ cycloalkyl group,a substituted or unsubstituted C₅-C₆₀ aryl group, a substituted orunsubstituted C₅-C₆₀ aryloxy group, a substituted or unsubstitutedC₅-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a (substituted or unsubstituted C₁-C₆₀ alkyl)amino group, adi(substituted or unsubstituted C₁-C₆₀ alkyl) amino group, or a(substituted or unsubstituted C₅-C₆₀ aryl)amino group or adi(substituted or unsubstituted C₅-C₆₀ aryl)amino group. One, two,three, four, five, or six groups selected from R₂₀ through R₃₉ may bethe binding site to Ar₂ (represented by Formula 2). For example, one,two, three, or four groups selected from R₂₀ through R₃₉ above may bethe binding site to Ar₂ (represented by Formula 2).

For example, R₂₀ through R₃₉ may each independently be a binding site toAr₂ (represented by Formula 2); hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxylic acid group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₂-C₂₀ alkenyl group, a substituted orunsubstituted C₂-C₂₀ alkynyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted C₁-C₂₀ alkylthio group, asubstituted or unsubstituted C₃-C₂₀ cycloalkyl group, a substituted orunsubstituted C₅-C₂₀ aryl group, a substituted or unsubstituted C₅-C₂₀aryloxy group, a substituted or unsubstituted C₅-C₂₀ arylthio group, asubstituted or unsubstituted C₂-C₂₀ heteroaryl group, a (substituted orunsubstituted C₁-C₂₀ alkyl)amino group, a di(substituted orunsubstituted C₁-C₂₀ alkyl) amino group, or a (substituted orunsubstituted C₅-C₂₀ aryl)amino group or a di(substituted orunsubstituted C₅-C₂₀ aryl)amino group. One, two, three, four, five, orsix groups selected from R₂₀ through R₃₉ may be the binding site to Ar₂(represented by Formula 2).

For example, R₂₀ through R₃₉ may each independently be one of a bindingsite to Ar₂ (represented by Formula 2), hydrogen; deuterium; a halogenatom; a hydroxyl group; a cyano group; a nitro group; an amino group; anamidino group; hydrazine; hydrazone; a carboxylic acid group or a saltthereof; a sulfonic acid group or a salt thereof; a phosphoric acidgroup or a salt thereof; a C₁-C₁₀ alkyl group; a C₁-C₁₀ alkoxy group; aC₁-C₁₀ alkylthio group; a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, anda C₁-C₁₀ alkylthio group substituted with one or more of deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxylic acid groupor a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; a phenyl group; a naphthylgroup; a fluorenyl group; a phenanthrenyl group; an anthryl group; apyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenylgroup, and a chrysenyl group substituted with one or more of deuterium,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxylic acid groupor a salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, and a C₁-C₁₀ alkylthio group; an indolyl group; a benzoimidazolylgroup; a carbazolyl group; an imidazolyl group; an imidazolinyl group;an imidazopyridinyl group; an imidazopyrimidinyl group; a pyridinylgroup; a pyrimidinyl group; a triazinyl group; a quinolinyl group; anindolyl group, a benzoimidazolyl group, a carbazolyl group, animidazolyl group, an imidazolinyl group, an imidazopyridinyl group, animidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group, and a quinolinyl group substituted with one or more ofdeuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthio group, a phenyl group,and a naphthyl group; a di(C₁-C₁₀ alkyl)amino group; or a di(C₆-C₂₀aryl)amino group, where the C₆-C₂₀ aryl group is a phenyl group, anaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthrylgroup, a pyrenyl group, or a chrysenyl group. One, two, three, four,five, or six groups selected from R₂₀ through R₃₉ may be the bindingsite to Ar₂ (represented by Formula 2).

For example, Ar₁ may be represented by any one of Formula 3A-1 throughFormula 3G-1, but is not limited thereto.

In the above Formula 3A-1 through 3G-1, R₂₀ through R₂₅ may eachindependently be a binding site to Ar₂ (represented by Formula 2);hydrogen, deuterium; a halogen atom; a hydroxyl group; a cyano group; anitro group; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkylgroup; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group substitutedwith one or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, and a phosphoric acid group or a salt thereof;a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenylgroup; an anthryl group; a pyrenyl group; a chrysenyl group; a phenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthryl group, a pyrenyl group, and a chrysenyl group substituted withone or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group;an indolyl group; a benzoimidazolyl group; a carbazolylgroup; animidazolyl group; an imidazolinyl group; an imidazopyridinyl group; animidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; atriazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolylgroup, a carbazolyl group, an imidazolyl group, an imidazolinyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, and a quinolinyl groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthiogroup, a phenyl group, and a naphthyl group; a di(C₁-C₁₀ alkyl) aminogroup; and a di(C₆-C₂₀ aryl)amino group, where the C₆-C₂₀ aryl group isa phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthryl group, a pyrenyl group, or a chrysenyl group. Also, i)at least one of R₂₀ through R₂₃ in Formulae 3A-1 and 3C-1 may be abinding site to Ar₂ (represented by Formula 2), ii) at least one of R₂₄through R₂₅ in Formula 3A-2 may be a binding site to Ar₂ (represented byFormula 2), iii) at least one of R₂₀ through R₂₁ in Formulae 3B-1, 3D-1,3E-1, 3F-1, and 3G-1 may be a binding site to Ar₂ (represented byFormula 2), and iv) at least one of R₂₂ through R₂₃ in Formulae 3B-2,3D-2, 3E-2, and 3F-2 may be a binding site to Ar₂ (represented byFormula 2).

According to an embodiment, Ar₁ may be represented by Formula 3A-1 or3B-1, but is not limited thereto.

X₁ in Formula 2 may be N(R₁₁), B(R₁₁), or Si(R₁₁)(R₁₂), wherein R₁₁ andR₁₂ may each independently be hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxylic acid group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₂-C₂₀ alkenyl group, a substituted orunsubstituted C₂-C₂₀ alkynyl group, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted pentalenyl group, asubstituted or unsubstituted indenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted azulenylgroup, a substituted or unsubstituted heptalenyl group, a substituted orunsubstituted indacenyl group, a substituted or unsubstitutedacenaphthyl group, a substituted or unsubstituted fluorenyl group, asubstituted or unsubstituted phenalenyl group, a substituted orunsubstituted phenanthrenyl group, a substituted or unsubstitutedanthryl group, a substituted or unsubstituted fluoranthenyl group, asubstituted or unsubstituted triphenylenyl group, a substituted orunsubstituted pyrenyl group, a substituted or unsubstituted chrysenylgroup, a substituted or unsubstituted naphthacenyl group, a substitutedor unsubstituted picenyl group, a substituted or unsubstituted perylenylgroup, a substituted or unsubstituted pentaphenyl group, a substitutedor unsubstituted hexacenyl group, a substituted or unsubstitutedpyrrolyl group, a substituted or unsubstituted pyrazolyl group, asubstituted or unsubstituted imidazolyl group, a substituted orunsubstituted imidazolinyl group, a substituted or unsubstitutedimidazopyridinyl group, a substituted or unsubstitutedimidazopyrimidinyl group, a substituted or unsubstituted pyridinylgroup, a substituted or unsubstituted pyrazinyl group, a substituted orunsubstituted pyrimidinyl group, a substituted or unsubstituted indolylgroup, a substituted or unsubstituted purinyl group, a substituted orunsubstituted quinolinyl group, a substituted or unsubstitutedphthalazinyl group, a substituted or unsubstituted indolizinyl group, asubstituted or unsubstituted naphthyridinyl group, a substituted orunsubstituted quinazolinyl group, a substituted or unsubstitutedcinnolinyl group, a substituted or unsubstituted indazolyl group, asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted phenazinyl group, a substituted or unsubstitutedphenanthridinyl group, a substituted or unsubstituted pyranyl group, asubstituted or unsubstituted chromenyl group, a substituted orunsubstituted furanyl group, a substituted or unsubstituted benzofuranylgroup, a substituted or unsubstituted thiophenyl group, a substituted orunsubstituted benzothiophenyl group, a substituted or unsubstitutedisothiazolyl group, a substituted or unsubstituted benzoimidazolylgroup, a substituted or unsubstituted isoxazolyl group, a substituted orunsubstituted dibenzothiophenyl group, a substituted or unsubstituteddibenzopuranyl group, a substituted or unsubstituted triazinyl group, ora substituted or unsubstituted oxadiazolyl group.

For example, X₁ in Formula 2 may be N(R₁₁), B(R₁₁), or Si(R₁₁)(R₁₂), andR₁₁ and R₁₂ may each independently be represented by any one of Formulae4A through 4H.

In Formulae 4A through 4F, Z₁ through Z₇ may each independently behydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; anitro group; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkylgroup; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group substitutedwith one or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, and a phosphoric acid group or a salt thereof;a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenylgroup; an anthryl group; a pyrenyl group; a chrysenyl group; a phenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthryl group, a pyrenyl group, and a chrysenyl group substituted withone or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group;an indolyl group; a benzoimidazolyl group; a carbazolyl group; animidazolyl group; an imidazolinyl group; an imidazopyridinyl group; animidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; atriazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolylgroup, a carbazolyl group, an imidazolyl group, an imidazolinyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, and a quinolinyl groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthiogroup, a phenyl group, and a naphthyl group; a di(C₁-C₁₀ alkyl) aminogroup; and a di(C₆-C₂₀ aryl)amino group, the C₆-C₂₀ aryl group may be aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthryl group, a pyrenyl group, or a chrysenyl group.

In Formula 2, X₁ may be O or S. X₂ in Formula 2 may be a single bond or—[C(R₁₅)(R₁₆)]_(n)—, where n is 1 or 2. For a detailed description ofR₁₅ and R₁₆, refer to the description of R₁₁. For example, R₁₅ and R₁₆may be hydrogen.

According to an embodiment, X₂ in Formula 2 may be a single bond.

In Formula 2, L₁ may be a single bond, a substituted or unsubstitutedphenylene group, a substituted or unsubstituted pentalenylene group, asubstituted or unsubstituted indenylene group, a substituted orunsubstituted naphthylene group, a substituted or unsubstitutedazulenylene group, a substituted or unsubstituted heptalenylene group, asubstituted or unsubstituted indacenylene group, a substituted orunsubstituted acenaphthylene group, a substituted or unsubstitutedfluorenylene group, a substituted or unsubstituted phenalenylene group,a substituted or unsubstituted phenanthrenylene group, a substituted orunsubstituted anthrylene group, a substituted or unsubstitutedfluoranthenylene group, a substituted or unsubstituted triphenylenylenegroup, a substituted or unsubstituted pyrenylene group, a substituted orunsubstituted chrysenylene group, a substituted or unsubstitutednaphthacenylene group, a substituted or unsubstituted pycenylene group,a substituted or unsubstituted perylenylene group, a substituted orunsubstituted pentacenylene group, a substituted or unsubstitutedhexacenylene group, a substituted or unsubstituted pyrrolylene group, asubstituted or unsubstituted pyrazolylene group, a substituted orunsubstituted imidazolylene group, a substituted or unsubstitutedimidazolinylene group, a substituted or unsubstitutedimidazopyridinylene group, a substituted or unsubstitutedimidazopyrimidinylene group, a substituted or unsubstituted pyridinylenegroup, a substituted or unsubstituted pyrazinylene group, a substitutedor unsubstituted pyrimidinylene group, a substituted or unsubstitutedindolylene group, a substituted or unsubstituted purinyl group, asubstituted or unsubstituted quinolinyl group, a substituted orunsubstituted phthalazinyl group, a substituted or unsubstitutedindolizinylene group, a substituted or unsubstituted naphthyridinylenegroup, a substituted or unsubstituted quinazolinylene group, asubstituted or unsubstituted cinnolinylene group, a substituted orunsubstituted indazolylene group, a substituted or unsubstitutedcarbazolylene group, a substituted or unsubstituted phenazinylene group,a substituted or unsubstituted phenanthridinylene group, a substitutedor unsubstituted pyranylene group, a substituted or unsubstitutedchromenylene group, a substituted or unsubstituted furanylene group, asubstituted or unsubstituted benzofuranylene group, a substituted orunsubstituted thiophenylene group, a substituted or unsubstitutedbenzothiophenylene group, a substituted or unsubstituted isothiazolylenegroup, a substituted or unsubstituted benzoimidazolylene group, asubstituted or unsubstituted isoxazolylene group, a substituted orunsubstituted dibenzothiophenylene group, a substituted or unsubstituteddibenzofuranylene group, a substituted or unsubstituted triazinylenegroup, or a substituted or unsubstituted oxadiazolylene group.

For example, L₁ may be a single bond, a substituted or unsubstitutedphenylene group, a substituted or unsubstituted naphthylene group, asubstituted or unsubstituted anthrylene group, a substituted orunsubstituted pyridinylene group, or a substituted or unsubstitutedquinolinylene group, but is not limited thereto.

For example, L₁ in Formula 2 may be a single bond or any one fromFormulae 5A through 5K below:

In Formulae 5A through 5K, Z₁₁ through Z₁₆ may each independently be oneof hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group;a nitro group; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkylgroup; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group substitutedwith one or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, and a phosphoric acid group or a salt thereof;a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenylgroup; an anthryl group; a pyrenyl group; a chrysenyl group; a phenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthryl group, a pyrenyl group, and a chrysenyl group substituted withone or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group;an indolyl group; a benzoimidazolyl group; a carbazolyl group; animidazolyl group; an imidazolynyl group; an imidazopyridinyl group; animidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; atriazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolylgroup, a carbazolyl group, an imidazolyl group, an imidazolinyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, and a quinolinyl groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthiogroup, a phenyl group, and a naphthyl group; a di(C₁-C₁₀ alkyl)aminogroup; and a di(C₆-C₂₀ aryl)amino group, where the C₆-C₂₀ aryl group maybe a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthryl group, a pyrenyl group, or a chrysenyl group.

For example, Ar₂ may be represented by any one of Formulae 2A through 2Kbelow:

In Formulae 2A through 2F, X₁, L₁, R₁ through R₃, a, and * are asdescribed above. R₄₀ through R₅₁ may each independently be one ofhydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; anitro group; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkylgroup; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group substitutedwith one or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, and a phosphoric acid group or a salt thereof;a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenylgroup; an anthryl group; a pyrenyl group; a chrysenyl group; a phenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthryl group, a pyrenyl group, and a chrysenyl group substituted withone or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group;an indolyl group; a benzoimidazolyl group; a carbazolyl group; animidazolyl group; an imidazolinyl group; an imidazopyridinyl group; animidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; atriazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolylgroup, a carbazolyl group, an imidazolyl group, an imidazolinyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, and a quinolinyl groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthiogroup, a phenyl group, and a naphthyl group; a di(C₁-C₁₀ alkyl) aminogroup; and a di(C₆-C₂₀ aryl)amino group, where the C₆-C₂₀ aryl group maybe a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthryl group, a pyrenyl group, or a chrysenyl group.

For example, R₄₀ through R₅₁ may each independently be one of hydrogen;deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitrogroup; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkyl; aC₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; and a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group substituted with oneor more of deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, hydrazine, hydrazone, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, and a phosphoric acid group or a salt thereof, but is notlimited thereto.

In Formula 2, R₁ through R₃ may each independently be one of hydrogen;deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitrogroup; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkylgroup; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; and a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof.

According to an embodiment, Ar₂ may be represented by Formula 2-1 below,but is not limited thereto:

In Formula 2-1, L₁, R₁ through R₃, a, Cy and Z₁ through Z₅ are asdescribed above.

In some embodiments of the condensed-cyclic compound, Ar₁ in Formula 1may be one of Formulae 3A through 3G; q in Formula 1 may be one of 1through 4; and Ar₂ may be a compound represented by one of Formulae 2Athrough 2K.

In some embodiments of the condensed-cyclic compound, Ar₁ in Formula 1may be one of Formulae 3A-1 through 3G-1; q in Formula 1 may be one of 1through 4; X₁ in Formula 2 may be N(R₁₁), B(R₁₁), or Si(R₁₁)(R₁₂), andR₁₁ and R₁₂ may each independently be represented by one of Formulae 4Athrough 4H; X₂ in Formula 2 may be a single bond; Cy in Formula 2 may bea substituted or unsubstituted C₆ cycloalkane (here, the substitutedcycloalkane is as described above with respect to R₄₀); and L₁ inFormula 2 may be a compound represented by Formulae 5A through 5K.

Also, in some embodiments of the condensed-cyclic compound, Ar₁ inFormula 1 may be Formula 3A-1 or 3B-1; q in Formula 1 may be one of 1through 4; and Ar₂ may be Formula 2-1.

In some embodiments, the condensed-cyclic compound may be any one ofCompounds 8 through 2000 represented by Formulae 8 through 2000, but isnot limited thereto:

The condensed-cyclic compound represented by Formula 1 includes Ar₂represented by Formula 2.

In Formula 2, a benzene ring and Cy are fused to each other with X₁ andX₂ therebetween. For example, when X₁ is N(R₁₁) and X₂ is a single bond,indoline may be formed in Formula 2 (see Formula 2(1) as below). Theindoline may improve the light-emitting efficiency of the organic lightemitting diode including the condensed-cyclic compound. Thus, thecondensed-cyclic compound including Formula 2 may provide goodlight-emitting efficiency.

Moreover, Cy in Formula 2 is a saturated ring. The electron donorstrength of such Cy is weaker than that of an unsaturated ring (forexample, benzene) where electrons are delocalized. By using thecondensed-cyclic compound including Formula 2 including Cy, emissionwavelengths in the deep-blue region may be obtained. The benzene ring ofFormula 2 is bound to Ar₁ with L₁ in the middle. Therefore, the electrondonor strength of the condensed-cyclic compound becomes weaker thanbefore and thus an energy gap is increased. As a result, deep-blue lightemission may be possible. For example, in a compound where Ar₁ isdirectly bound to X₁, electron donor strength is increased and thus theenergy gap is decreased. As a result, light emission wavelengthred-shifts and green light emission may be possible.

When an organic light-emitting diode (OLED) including thecondensed-cyclic compound between a pair of electrodes (anode andcathode) is operated, the OLED may exhibit good driving voltage,efficiency, brightness and life-time characteristics due to thecondensed-cyclic compound having high heat resistance to Joule's heatgenerated between organic layers positioned between the pair ofelectrodes or between one of the organic layers and one of theelectrodes.

The condensed-cyclic compound of Formula 1 may be synthesized using anyknown organic synthesis method. The synthesis method of thecondensed-cyclic compound of Formula 1 may be readily understood bythose of ordinary skill in the art with reference to the providedExamples, which are described below.

The condensed-cyclic compound of Formula 1 may be used between a pair ofelectrodes of an OLED. For example, the condensed-cyclic compound ofFormula 1 may be used in an emission layer and/or a layer between ananode and the emission layer (for example, a hole injection layer (HIL),a hole transport layer (HTL), or a functional layer having holeinjection and hole transport abilities).

According to another embodiment of the present invention, there isprovided an OLED including a first electrode, a second electrode facingthe first electrode, and an organic layer between the first electrodeand the second electrode, wherein the organic layer includes at leastone of the condensed-cyclic compounds of Formula 1 described above.

As used herein, the expression “(the organic layer) may include at leastone of the condensed-cyclic compounds of Formula 1” may be understood as“(the organic layer) may include one within a range of thecondensed-cyclic compounds of Formula 1 or two or more of thecondensed-cyclic compounds that are different from each other within therange of Formula 1”.

For example, the organic layer may include only Compound 38 as thecondensed-cyclic compound. Here, Compound 38 may be included in theemission layer of an OLED. In another embodiment, the organic layer mayinclude Compound 38 and Compound 262 as the condensed-cyclic compounds.Here, Compound 38 and Compound 262 may be included in the same layer(for example, Compound 38 and Compound 262 may be included in theemission layer) or may be included in different layers (for example,Compound 38 may be included in the emission layer and Compound 262 maybe included in the electron transport layer).

The organic layer may include at least one of a HIL, a HTL, a functionallayer (hereinafter, referred to as “H-functional layer”) having holeinjection and hole transport abilities, a buffer layer, an electronblocking layer (EBL), an emission layer (EML), a hole blocking layer(HBL), an electron transport layer (ETL), an electron injection layer(EIL), and a functional layer (hereinafter, referred to as “E-functionallayer”) having electron transport and electron injection abilities.

The term “organic layer” used herein refers to a single layer ormultiple layers positioned between the first electrode and the secondelectrode of an OLED.

The organic layer includes an EML including the condensed-cycliccompound of Formula 1. In some embodiments, the organic layer mayinclude at least one of a HIL, a HTL, and a H-functional layer, and thecondensed-cyclic compound of Formula 1 may be included in at least oneof the HIL, the HTL, and the H-functional layer.

The condensed-cyclic compound of Formula 1 included in the EML may serveas a dopant. For example, the condensed-cyclic compound of Formula 1 mayserve as a blue dopant for emitting blue light. In other embodiments,the condensed-cyclic compound of Formula 1 included in the EML may serveas a fluorescent or phosphorescent host for emitting red light, greenlight, or blue light.

FIG. 1 is a schematic cross-sectional view of an OLED 10 according to anembodiment of the present invention. Hereinafter, a structure and amanufacturing method of an OLED will be described in more detail withreference to FIG. 1.

The substrate 11 may be a substrate used in a conventional OLED and maybe a glass substrate or a transparent plastic substrate having goodmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and waterproofness.

A first electrode 13 may be formed by applying a first electrodematerial on the substrate 11 by deposition or sputtering. When the firstelectrode 13 is an anode, the first electrode material may be selectedfrom materials having a high work function so as to facilitate holeinjection. The first electrode 13 may be a reflective electrode or atransparent electrode. Examples of the first electrode material mayinclude indium-tin oxide (ITO), indium-zinc oxide (IZO), tin oxide(SnO₂), and zinc oxide (ZnO). Also, when magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) is used as the first electrode material, thefirst electrode 13 may be formed as a reflective electrode.

The first electrode 13 may have a single layer or two or more layers.For example, the first electrode 13 may have a three-layered structuredof ITO/Ag/ITO, but is not limited thereto.

An organic layer 15 may be formed on the first electrode 13.

The organic layer 15 may include a HIL, a HTL, a buffer layer, an EML,an ETL, and an EIT.

The HIL may be formed on the first electrode 13 using various methodssuch as vacuum deposition, spin coating, casting, or LB deposition.

When the HIL is formed using vacuum deposition, the depositionconditions may vary according to the compound used as the material forforming the HIL, the structure of the desired HIL, and the thermalcharacteristics. For example, the deposition conditions may be, but arenot limited thereto, a deposition temperature of about 100 to about 500°C., a degree of vacuum of about 10⁻⁸ to about 10⁻³ torr, and adeposition speed of about 0.01 to about 100 Å/sec.

When the HIL is formed by spin coating, the coating conditions may varyaccording to the compound used as the material for forming the HIL, thestructure of the desired HIL, and the thermal characteristics. Forexample, the coating conditions may be, but are not limited to, acoating speed of about 2,000 to about 5,000 rpm and a heat treatmenttemperature for removing solvent after coating of about 80 to about 200°C.

The material for forming the HIL may be any known hole injectionmaterial. Examples of hole injection materials include, but are notlimited thereto,N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), a phthalocyanine compound such as copper phthalocyanine,4,4′,4″-tris (3-methylphenylphenylamino)triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine(NPB),4,4′4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA),Polyaniline/Dodecylbenzenesulfonic acid (Pani/DBSA),Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) (PEDOT/PSS),Polyaniline/Camphor sulfonicacid (Pani/CSA), orPolyaniline/Poly(4-styrenesulfonate) (PANI/PSS).

The thickness of the HIL may be in a range of about 100 Å to about10,000 Å, for example, in a range of about 100 Å to about 1,000 Å. Whenthe thickness of the HIL is within these ranges, satisfactory holeinjection properties may be obtained without a substantial increase indriving voltage.

Next, the HTL may be formed on the HIL using various methods such asvacuum deposition, spin coating, casting, or LB deposition. When the HTLis formed by vacuum deposition or spin coating, the deposition orcoating conditions may vary according to the compound used. However, ingeneral, the conditions may be almost the same as the conditionsdescribed above for forming the HIL.

The material for forming the HTL may be any known hole transportingmaterial. Examples of the hole transporting material include carbazolederivatives such as N-phenylcarbazole and polyvinylcarbazole,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),α-NPD(N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-2,2′-dimethylbenzidine)and N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), but are notlimited thereto.

The thickness of the HTL may be in a range of about 50 Å to about 2,000Å, for example, in a range of about 100 Å to about 1,500 Å. When thethickness of the HTL is within these ranges, satisfactory hole transportproperties may be obtained without a substantial increase in drivingvoltage.

The H-functional layer (which is a functional layer having holeinjection and hole transport abilities) may include one or more of thehole injection materials described above and the HTL materials. Thethickness of the H functional layer may be in a range of about 50 Å toabout 10,000 Å, for example, in a range of about 100 Å to about 1,000 Å.When the thickness of the H-functional layer is within these ranges,satisfactory hole injection and transport properties may be obtainedwithout a substantial increase in driving voltage.

At least one of the HIL, the HTL, and the H-functional layer may furtherinclude a charge-generating material in order to improve theconductivity of the layer and the hole injection material, the holetransport material, and/or the material having hole injection and holetransport functions described above.

The charge-generating material may be, for example, a p-dopant. Examplesof the p-dopant may include, but are not limited to, quinone derivativessuch as tetracyanoquinodimethane (TCNQ), and2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4TCNQ); metaloxides such as a tungsten oxide and a molybdenum oxide; andcyano-containing compounds such as Compound 200 below and the like.

When the HIL, the HTL, or the H-functional layer further include thecharge-generating material, the charge-generating material may behomogeneously or inhomogeneously dispersed in these layers.

A buffer layer may be disposed between at least one of the HIL, the HTL,or the H-functional layer and the EML. The buffer layer may serve toimprove efficiency by compensating for an optical resonance distanceaccording to the wavelength of light emitted from the EML. The bufferlayer may include the hole injection material and the hole transportmaterial. In some embodiments, the buffer layer may include the samematerial included in the HIL, the HTL, or the H-functional layer formedunder the buffer layer.

Subsequently, the EML may be formed on the HTL, the H-functional layer,or the buffer layer using various methods such as vacuum deposition,spin coating, casting, or LB deposition. When the EML is formed byvacuum deposition or spin coating, the deposition or coating conditionsmay vary according to the compound used. However, in general, theconditions may be almost the same as the conditions described above forforming the HIL.

The EML may include at least one of the condensed-cyclic compounds.

The EML may further include a host and the condensed-cyclic compound.

Examples of the host may include, but are not limited to, Alq₃,4,4′-N,N′-dicabazole-biphenyl (CBP), poly(n-vinylcabazole) (PVK),9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA,1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-tert-butyl-9,10-di(naphth-2-yl) anthracene (TBADN), E3,distyrylarylene (DSA), dmCBP (refer to Formula below) and Compounds 501through 509 below.

Alternatively, the host may be an anthracene-based compound representedby Formula 60 below:

In Formula 60, Ar₁₁ and Ar₁₂ may each independently be a substituted orunsubstituted C₅-C₆₀ arylene group; Ar₁₃ and Ar₁₄ may each independentlybe a substituted or unsubstituted C₁-C₁₀ alkyl group or a substituted orunsubstituted C₅-C₆₀ aryl group; and e and f may each independently bean integer of 0 to 5.

For example, in Formula 60, Ar₁₁ and Ar₁₂ may each independently be aphenylene group; or a phenylene group that is substituted with one ormore of a phenyl group, a naphthyl group, and an anthryl group, but arenot limited thereto. In Formula 60, e and f may each independently be 0,1, or 2.

In Formula 60, Ar₁₃ and Ar₁₄ may each independently be one of a C₁-C₁₀alkyl group that is substituted with one or more of a phenyl group, anaphthyl group, or an anthryl group; a phenyl group; a naphthyl group;an anthryl group; a pyrenyl group; a phenanthrenyl group; and a phenylgroup, a naphthyl group, an anthryl group, a pyrenyl group, or aphenanthrenyl group that is substituted with one or more of deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxylic acid groupor a salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; but are notlimited thereto.

For example, in Formula 60, Ar₁₁ and Ar₁₂ may each independently be aphenylene group; or a phenylene group that is substituted with one ormore of a phenyl group, a naphthyl group, and an anthryl group; e and fmay each independently be 0, 1, or 2; and Ar₁₃ and Ar₁₄ may eachindependently be one selected from a C₁-C₁₀ alkyl group that issubstituted with one or more of a phenyl group, a naphthyl group, and ananthryl group; a phenyl group; a naphthyl group; an anthryl group; apyrenyl group; and a phenanthrenyl group, but are not limited thereto.

For example, the anthracene-based compound of Formula 60 may be one ofCompounds BH01 through BH39 below, but are not limited thereto:

To manufacture a full-color OLED, a red EML and a green EML may befurther patterned.

When the OLED is a full-color OLED, the EML may be patterned with a redEML, a green EML, or a blue EML. Here, the condensed-cyclic compound ofFormula 1 described above may be included as a blue fluorescent dopantin the blue EML. At least one of the red EML, the green EML, and theblue EML may include the dopant below (ppy=phenylpyridine).

For example, the compounds below may be used as a blue dopant, but arenot limited thereto:

For example, the compounds below may be used as a red dopant, but arenot limited thereto:

For example, the compounds below may be used as a green dopant, but arenot limited thereto.

Examples of a dopant included in the EML include the Pt-complexesdescribed below, but are not limited thereto:

Moreover, examples of a dopant included in the EML include theOs-complexes described below, but are not limited thereto:

When the EML includes a host and a dopant, the amount of the dopant inthe EML may generally be in a range of about 0.01 to about 15 parts byweight based on 100 parts by weight of the host, but are not limitedthereto.

The thickness of the EML may be in a range of about 100 Å to about 1,000Å, for example, in a range of about 200 Å to about 600 Å. When thethickness of the EML is within this range, good luminescent propertiesmay be obtained without a substantial increase in driving voltage.

Next, the ETL is formed on the EML using various methods such as vacuumdeposition, spin coating, or casting. When the ETL is formed usingvacuum deposition or spin coating, the deposition or coating conditionsmay vary according to the compound used. However, in general, theconditions may be almost the same as the conditions described above forforming the HIL. The material for forming the ETL may be used to stablytransport electrons injected from the cathode and may be any knownelectron transporting material. Examples of the electron transportingmaterial may include, but are not limited to, a quinoline derivativesuch as tris(8-quinolinolate)aluminum (Alq₃), TAZ, Balq, berylliumbis(benzoquinolin-10-olate (Bebq₂), AND, Compound 201 below, andCompound 202 below.

The thickness of the ETL may be in a range of about 100 Å to about 1,000Å, for example, in a range of about 150 Å to about 500 Å. When thethickness of the ETL is within this range, satisfactory electrontransport properties may be obtained without a substantial increase indriving voltage.

In addition, the ETL may further include a known electron transportingorganic compound and a metal-containing material.

The metal-containing material may include a Li-complex. Examples of theLi-complex may include lithium quinolate (Liq) and Compound 203 below:

Also, the EIL, which facilitates electron injection from the cathode,may be deposited on the ETL, and the material for forming the EIL is notparticularly limited. The material for forming the EIL may include anyknown material for forming an EIL, such as LiF, NaCl, CsF, Li₂O, or BaO.The deposition conditions of the EIL may vary according the compoundused. However, in general, the conditions may be almost the same as theconditions described above for forming the HIL.

The thickness of the EIL may be in a range of about 1 Å to about 100 Å,for example, in a range of about 3 Å to about 90 Å. When the thicknessof the EIL is within these ranges, satisfactory electron injectionproperties may be obtained without a substantial increase in drivingvoltage.

The second electrode 17 is formed on the organic layer 15. The secondelectrode 17 may be a cathode, which is an electron injection electrode.Here, a metal for forming the second electrode 17 may include a metalhaving a low work function, such as a metal, an alloy, an electricallyconductive compound, and a mixture thereof. For example, the secondelectrode 17 may be formed as a thin film using lithium (Li), magnesium(Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag), thus beingtransparent. In order to obtain a top-emission type OLED, the secondelectrode 17 may be formed as a transparent electrode using ITO or IZO.

As described above, the OLED is described with reference to FIG. 1, butis not limited thereto.

When a phosphorescent dopant is used to form the EML, a HBL may beformed between the HTL and the EML or the H-functional layer and the EMLin order to prevent diffusion of triplet excitons or holes into an ETL.The HBL may be formed using various methods such as vacuum deposition,spin coating, casting, LB deposition or the like. When the HBL is formedusing vacuum deposition or spin coating, the deposition or coatingconditions may vary according to the compound used. However, in general,the conditions may be almost the same as the conditions described abovefor forming the HIL. Any material that is commonly used to form a HBLmay be used. Examples of the material for forming the HBL include anoxadiazole derivative, a triazole derivative, and a phenanthrolinederivative, but are not limited thereto. For example, BCP below may beused as a HBL material.

The thickness of the HBL may be in a range of about 20 Å to about 1000Å, for example, about 30 Å to about 300 Å. When the thickness of the HBLis within these ranges, the HBL may achieve good hole blocking abilitywithout substantially increasing driving voltage.

As used herein, specific nonlimiting examples of an unsubstituted C₁-C₆₀alkyl group (or a C₁-C₆₀ alkyl group) include a linear or branchedC₁-C₆₀ alkyl group such as a methyl, an ethyl, a propyl, an isobutyl, asec-butyl, pentyl, an iso-amyl, or a hexyl. The substituted C₁-C₆₀ alkylgroup may be the unsubstituted C₁-C₆₀ alkyl group in which one or morehydrogen atoms are substituted with deuterium, a halogen atom, a hydroxygroup, a nitro group, a cyano group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, or a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₆-C₆₀ aryl group, a C₂-C₆₀ heteroaryl group,—N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅) (here, Q₁₁ through Q₁₅ are eachindependently selected from hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₅-C₆₀ aryl group, and a C₂-C₆₀heteroaryl group).

As used herein, the unsubstituted C₁-C₆₀ alkoxy group (or a C₁-C₆₀alkoxy group) has the formula —OA (in this regard, A is theunsubstituted C₁-C₆₀ alkyl group as described above) and examplesthereof include methoxy, ethoxy, isopropyloxy, and the like. Thesubstituted C₁-C₆₀ alkoxy group includes the unsubstituted C₁-C₆₀ alkoxygroup in which at least one or more hydrogen atoms is substituted withone or more of the substituents described above with reference to theC₁-C₆₀ alkyl group.

As used herein, the unsubstituted C₁-C₆₀ alkylthio group (or a C₁-C₆₀alkylthio group) has the formula—SA (in this regard, A is theunsubstituted C₁-C₆₀ alkyl group as described above). The substitutedC₁-C₆₀ alkylthio group is the unsubstituted C₁-C₆₀ alkylthio group inwhich at least one or more hydrogen atoms is substituted with one ormore of the substituents described above with reference to the C₁-C₆₀alkyl group.

As used herein, the unsubstituted C₂-C₆₀ alkenyl group is interpreted tocontain one or more carbon-carbon double bonds in the center or at aterminal end of the unsubstituted C₂-C₆₀ alkyl group. Examples of theunsubstituted C₂-C₆₀ alkenyl group include ethenyl, propenyl, butenyl,and the like. The substituted C₂-C₆₀ alkenyl group is the unsubstitutedC₂-C₆₀ alkenyl group in which at least one or more hydrogen atoms issubstituted with one or more of the substituents described above withreference to the C₁-C₆₀ alkyl group.

As used herein, the unsubstituted C₂-C₆₀ alkynyl group is interpreted tocontain one or more carbon-carbon triple bonds in the center or at aterminal end of the unsubstituted C₂-C₆₀ alkyl group defined above.Examples of the substituted C₂-C₆₀ alkynyl group include ethynyl,propynyl, and the like. The substituted C₂-C₆₀ alkynyl group is theunsubstituted C₂-C₆₀ alkynyl group in which at least one or morehydrogen atoms is substituted with one or more of the substituentsdescribed above with reference to the C₁-C₆₀ alkyl group.

As used herein, the unsubstituted C₅-C₆₀ aryl group may indicate amonovalent group having an aromatic carbocyclic system that has 5 to 60carbon atoms and one or more aromatic rings. The unsubstituted C₅-C₆₀arylene group may indicate a divalent group having an aromaticcarbocyclic system that has 5 to 60 carbon atoms and one or morearomatic rings. If each of the unsubstituted C₅-C₆₀ aryl group and theunsubstituted C₅-C₆₀ arylene group includes two or more rings, the ringsmay optionally be fused to each other. The substituted C₅-C₆₀ aryl groupand the substituted C₅-C₆₀ arylene group are the unsubstituted C₅-C₆₀aryl group and the unsubstituted C₅-C₆₀ arylene group, respectively, inwhich at least one hydrogen atom is substituted with one or more of thesubstituents described above with reference to the C₁-C₆₀ alkyl group.

Examples of the substituted or unsubstituted C₅-C₆₀ aryl group include aphenyl group, a C₁-C₁₀ alkylphenyl group (e.g., an ethylphenyl group), aC₁-C₁₀ alkylbiphenyl group (e.g., an ethylbiphenyl group), a halophenylgroup (e.g., o-, m-, or p-fluorophenyl group, dichlorophenyl group), adicyanophenyl group, a trifluoromethoxyphenyl group, o-, m-, or p-tolylgroup, o-, m-, or p-cumenyl, a mesityl group, a phenoxyphenyl group, a(α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a(N,N′-diphenyl)aminophenyl group, a pentalenyl group, an indenyl group,a naphthyl group, a halonaphthyl group (e.g., a fluoronaphthyl group), aC₁-C₁₀ alkylnaphthyl group (e.g., a methylnaphthyl group), a C₁-C₁₀alkoxynaphthyl group (e.g., a methoxynaphthyl group), a anthracenylgroup, an azulenyl group, a heptalenyl group, an acenaphthylenyl group,a phenalenyl group, a fluorenyl group, an anthraquinolyl group, amethylanthryl group, a phenanthryl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenylgroup, a perylenyl group, a chloroperylenyl group, a pentaphenyl group,a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, ahexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenylgroup, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group,and an ovalenyl group. Examples of the substituted C₅-C₆₀ aryl group maybe readily recognized by reference to the examples of the unsubstitutedC₅-C₆₀ aryl group described above and the substituents of thesubstituted C₁-C₆₀ alkyl group. Examples of the substituted orunsubstituted C₅-C₆₀ arylene group may be readily recognized byreference to the substituted or unsubstituted C₅-C₆₀ aryl groupdescribed above.

As used herein, the unsubstituted C₂-C₆₀ heteroaryl group indicates amonovalent group having at least one aromatic ring system includingcarbon rings and one or more hetero atoms selected from N, O, P, and S.The unsubstituted C₂-C₆₀ heteroarylene group indicates a divalent grouphaving at least one aromatic ring system including carbon rings and oneor more hetero atoms selected from N, O, P, and S. In this regard, ifthe C₂-C₆₀ heteroaryl group and the C₂-C₆₀ heteroarylene group eachindependently have two or more aromatic rings, the rings may optionallybe fused to each other. The substituted C₂-C₆₀ heteroaryl group and thesubstituted C₂-C₆₀ heteroarylene group are the unsubstituted C₂-C₆₀heteroaryl group and the unsubstituted C₂-C₆₀ heteroarylene group,respectively, in which one or more hydrogen atoms is substituted withone or more of the substituents described above with reference to theC₁-C₆₀ alkyl group.

Examples of the unsubstituted C₂-C₆₀ heteroaryl group include apyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, apyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinylgroup, a carbazolyl group, an indolyl group, a quinolinyl group, anisoquinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group,and an imidazopyrimidinyl group. Examples of the unsubstituted C₂-C₆₀heteroarylene group may be readily recognized by reference to theexamples of the unsubstituted C₂-C₆₀ heteroarylene group.

The substituted or unsubstituted C₅-C₆₀ aryloxy group has the formula—OA₂ where A₂ is the substituted or unsubstituted C₅-C₆₀ aryl group asdescribed above. The substituted or unsubstituted C₅-C₆₀ arylthio grouphas the formula—SA₃ where A₃ is the substituted or unsubstituted C₅-C₆₀aryl group described above.

Hereinafter, an OLED according to an embodiment of the present inventionwill now be described with reference to the following examples. However,these examples are presented for illustrative purposes only and are notintended to limit the scope of the invention.

EXAMPLE Synthesis Example 1 Synthesis of Compound 38 Synthesis ofIntermediate 1-a

Intermediate 1-a was synthesized according to Reaction Scheme 1 below:

50 g (0.462 mol) of phenylhydrazine and 170 ml of acetic acid were putinto a 500 ml round-bottom flask, and the temperature was raised to 60°C. 51.9 g (0.462 mol) of 2-methylcyclohexanone was dropped into theheated flask, and the mixture was refluxed for about 8 hours. After thereaction was completed, 100 ml of water was added to the mixture, andthe resultant mixture was made alkaline with sodium hydroxide. Then, theresultant solution was extracted with water and ethyl acetate toseparate an organic layer. The obtained organic layer was dried withanhydrous magnesium sulfate and concentrated under reduced pressure.Thereafter, the resulting product was purified by column chromatographyusing hexane and ethyl acetate as eluents. As a result, 72 g ofIntermediate 1-a was obtained (yield: 84%).

Synthesis of Intermediate 1-b

Intermediate 1-b was synthesized according to Reaction Scheme 2 below:

57 g (0.308 mol) of Intermediate 1-a was dissolved in 570 ml of toluenein a 2 L round-bottom flask in a nitrogen atmosphere, and thetemperature was then decreased to −10° C. 300 ml (0.474 mol) of 1.6Mmethyl lithium was slowly dropped into the resultant mixture and thereaction was carries out at −10° C. for 3 hours. Subsequently, water wasslowly added to the resultant mixture until the solution had noreactivity. The resultant solution was extracted with water and ethylacetate to separate the organic layer. The obtained organic layer wasdried with anhydrous magnesium sulfate and concentrated under reducedpressure. Thereafter, the resulting product was purified by columnchromatography using hexane and ethyl acetate as eluents. As a result,47 g of Intermediate 1-b was obtained (yield: 76%).

Synthesis of Intermediate 1-c

Intermediate 1-c was synthesized according to Reaction Scheme 3 below:

40 g (0.199 mol) of Intermediate 1-b, 48.6 g (0.238 mol) of iodobenzene,0.89 g (0.004 mol) oftris(dibenzylideneacetone)dipalladium(0)(Pd(dba)₃), 2.47 g (0.004 mol)of 2,2-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), 38.19 g (0.397mol) of sodium tertiarybutoxide, and 400 ml of toluene were added to a 1L round-bottom flask, and the mixture was refluxed for 8 hours andfiltered with celite. The filtrate was concentrated under reducedpressure. The resulting product was purified by column chromatographyusing hexane as the eluent. As a result, 44 g of Intermediate 1-c wasobtained (yield: 79%).

Synthesis of Intermediate 1-d

Intermediate 1-d was synthesized according to Reaction Scheme 4 below:

44 g (0.158 mol) of Intermediate 1-c and 130 ml of dimethylformamide wasput into a 500 ml round-bottom flask, and the temperature was thendecreased to 0° C. Subsequently, 25.2 g (0.142 mol) ofN-bromosuccinimide was dissolved in 220 ml of dimethylformamide, and thesolution was slowly added to the mixture. After the addition of thesolution was complete, the temperature was raised to room temperature,and the resultant mixture was stirred for 2 hours. Then, the resultantsolution was extracted with water and dichloromethane to separate theorganic layer. The obtained organic layer was dried with anhydrousmagnesium sulfate and concentrated under reduced pressure. Thereafter,the resulting product was crystallized with hexane and the crystalproduced therefrom was filtered. As a result, 45 g of Intermediate 1-dwas obtained (yield: 80%).

Synthesis of Intermediate 1-e

Intermediate 1-e was synthesized according to Reaction Scheme 5 below:

40 g (0.112 mol) of Intermediate 1-d, 34 g (0.134 mol) ofbis(pinacolato)diboron, 2.73 g (0.003 mol) of palladium(II) chloride(PdCl₂), 32.9 g (0.335 mol) of potassium acetate, and 480 ml of toluenewere put into a 1 L round-bottom flask, and the mixture was refluxed for8 hours and filtered with celite. The filtrate was concentrated underreduced pressure. Thereafter, the resulting product was purified bycolumn chromatography using hexane and ethyl acetate as eluents. As aresult, 26 g of Intermediate 1-e was obtained (yield: 58%).

Synthesis of Intermediate 1-f

Intermediate 1-f was synthesized according to Reaction Scheme 6 below:

21 g (0.053 mol) of Intermediate 1-e, 30 g (0.053 mol) of1-bromo-4-iodobenzene, 4.9 g (0.004 mol) ofTetrakis(triphenylphosphine)palladium(0) (Pd(pph)₄), 43.97 g (0.318 mol)of potassium carbonate, 150 ml of dioxane, 150 ml of toluene, and 60 mlof water were put into a 1 L round-bottom flask, and the mixture wasrefluxed. After the reaction was complete, the resultant solution wasextracted with water and ethyl acetate to separate the organic layer.The obtained organic layer was dried with anhydrous magnesium sulfateand concentrated under reduced pressure. Thereafter the resultingproduct was purified by column chromatography using hexane as theeluent. As a result, 18 g of Intermediate 1-f was obtained (yield: 76%).

Synthesis of Intermediate 1-g

Intermediate 1-g was synthesized according to Reaction Scheme 7 below:

25 g (0.059 mol) of Intermediate 1-f, 18 g (0.069 mol) ofbis(pinacolato)diboron, 1.4 g (0.002 mol) of PdCl₂, 17 g (0.174 mol) ofpotassium acetate, and 250 ml of toluene were put into a 500 mLround-bottom flask, and the mixture was refluxed for 8 hours. After thereaction was completed, the resultant mixture was filtered with celite,and the filtrate was concentrated under reduced pressure. Thereafter,the resulting product was purified by column chromatography using hexaneand ethyl acetate as eluents. As a result, 15 g of Intermediate 1-g wasobtained (yield: 54%).

Synthesis of Compound 38

Compound 38 was synthesized according to Reaction Scheme 8 below:

10.2 g (0.021 mol) of Intermediate 1-g, 5 g (0.018 mol) of1-bromopyrene, 0.8 g (0.001 mol) of Pd(pph)₄, 7.4 g (0.053 mol) ofpotassium carbonate, 25 ml of dioxane, 25 ml of toluene, and 10 ml ofwater were put into a 250 ml round-bottom flask, and the mixture wasrefluxed. After the reaction was completed, water and hexane were added,and the crystals produced therefrom were filtered. The crystals wererecrystallized, and 6.1 g of Compound 38 was obtained (yield 62%).

Molecular weight: 553.73

Elementary analysis: Calculated C, 91.10; H, 6.37; N, 2.53. Found C,91.13; H, 6.39; N, 2.48

1H NMR (CDCl₃): δ 8.2˜8.1 (m, 3H, Ar—H), δ 7.81˜7.72 (m, 6H, Ar—H), δ7.38˜6.8 (m, 12H, Ar—H), δ 1.59˜1.31 (m, 8H, CH₂—H), δ 1.31˜1.15 (d, 6H,CH₃—H)

Synthesis Example 2 Synthesis of Compound 262 Synthesis of Intermediate2-c

Intermediate 2-c was synthesized according to Reaction Scheme 9 below:

59 g of Intermediate 2-c was obtained (yield: 85.6%) in the same manneras in the Synthesis of Intermediate 1-c, except that1-bromo-3-fluorobenzene was used instead of iodobenzene.

Synthesis of Intermediate 2-d

Intermediate 2-d was synthesized according to Reaction Scheme 10 below:

42 g of Intermediate 2-d was obtained (yield: 84.4%) in the same manneras in the Synthesis of Intermediate 1-d, except that Intermediate 2-cwas used instead of Intermediate 1-c.

Synthesis of Intermediate 2-e

Intermediate 2-e was synthesized according to Reaction Scheme 11 below:

21 g of Intermediate 2-e was obtained (yield: 44.6%) in the same manneras in the Synthesis of Intermediate 1-e, except that Intermediate 2-dwas used instead of Intermediate 1-d.

Synthesis of Intermediate 2-h

Intermediate 2-h was synthesized according to Reaction Scheme 12 below:

50 g (0.247 mol) of pyrene was dissolved in 500 ml of chloroform in a 2L round-bottom flask, and the temperature was decreased to 0° C. Then, asolution of 158 g (0.989 mol) of bromine dissolved in 150 ml ofchloroform was slowly added to the flask, the temperature was slowlyraised to room temperature, and the resultant mixture was reacted for 8hours. After the reaction was complete, 100 ml of water was added andthe bromine was removed using sodium thiosulfate, and the crystalsformed therefrom were filtered and recrystallized. As a result, 97.5 gof Intermediate 2-h was obtained (76%).

Synthesis of Intermediate 2-i

Intermediate 2-i was synthesized according to Reaction Scheme 13 below:

50 g (0.097 mol) of Intermediate 2-h, 35.3 g (0.290 mol) ofphenylboronic acid, 4.5 g (0.004 mol) of Pd(pph)₄, 407.4 g (0.290 mol)of potassium carbonate, 250 ml of dioxane, 250 ml of toluene, and 100 mlof water were put into a 1 L round-bottom flask, and the mixture wasrefluxed. After the reaction was complete, water and hexane was added,and the crystals formed therefrom were filtered and recrystallized. As aresult, 37.3 g of Intermediate 2-i was obtained (yield: 76%).

Synthesis of Compound 262

Compound 262 was synthesized according to Reaction Scheme 14 below:

8.4 g of Compound 262 was obtained (yield: 59%) in the same manner as inthe Synthesis of Compound 38, except that Intermediate 2-i was usedinstead of 1-bromopyrene, and Intermediate 2-e was used instead ofIntermediate 1-g. Molecular weight: 723.92

Elementary analysis: Calculated C, 89.59; H, 5.85; F, 2.62; N, 1.93.Found C, 89.60; H, 5.93; F, 2.57; N, 1.90

¹H NMR (CDCl₃): δ 8.3˜8.2 (d, 2H, Ar—H), δ 7.80˜7.68 (m, 10H, Ar—H), δ7.43˜6.4 (m, 16H, Ar—H), δ 1.61˜1.33 (m, 8H, CH₂—H), δ 1.31˜1.15 (d, 6H,CH₃—H)

Synthesis Example 3 Synthesis of Compound 586 Synthesis of Intermediate3-a

Intermediate 3-a was synthesized according to Reaction Scheme 15 below:

64.1 g of Intermediate 3-a was obtained (yield: 81.4%) in the samemanner as in Synthesis of Intermediate 1-a, except that2-methylcyclopentanone was used instead of 2-methylcyclohexanone.

Synthesis of Intermediate 3-b

Intermediate 3-b was synthesized according to Reaction Scheme 16 below:

45.1 g of Intermediate 3-b was obtained (yield: 76.8%) in the samemanner as in the Synthesis of Intermediate 1-b, except that Intermediate3-a was used instead of Intermediate 1-a.

Synthesis of Intermediate 3-c

Intermediate 3-c was synthesized according to Reaction Scheme 17 below:

51.7 g of Intermediate 3-c was obtained (yield: 81.7%) in the samemanner as in the Synthesis of Intermediate 1-c, except that Intermediate3-b was used instead of Intermediate 1-b.

Synthesis of Intermediate 3-d

Intermediate 3-d was synthesized according to Reaction Scheme 18 below:

40.8 g of Intermediate 3-d was obtained (yield: 66.3%) in the samemanner as in the Synthesis of Intermediate 1-d, except that Intermediate3-c was used instead of Intermediate 1-c.

Synthesis of Intermediate 3-e

Intermediate 3-e was synthesized according to Reaction Scheme 19 below:

22.3 g of Intermediate 3-e was obtained (yield: 48.9%) in the samemanner as in the Synthesis of Intermediate 1-e, except that Intermediate3-d was used instead of Intermediate 1-d.

Synthesis of Intermediate 3-h

Intermediate 3-h was synthesized according to Reaction Scheme 20 below:

81.5 g of Intermediate 3-h was obtained (yield: 81.5%) in the samemanner as in the Synthesis of Intermediate 2-h, except that 177 g ofbromine was used instead of 158 g of bromine.

Synthesis of Compound 586

Compound 586 was synthesized according to Reaction Scheme 21 below:

10.2 g of Compound 586 was obtained (yield: 45%) in the same manner asin the Synthesis of Compound 38, except that Intermediate 3-h was usedinstead of 1-bromopyrene and Intermediate 3-e was used instead ofIntermediate 1-g. Molecular weight: 986.33

Elementary analysis: Calculated C, 88.89; H, 6.85; N, 4.26. Found C,88.91; H, 6.90; N, 4.19

¹H NMR (CDCl₃): δ 8.3˜8.1 (m, 3H, Ar—H), δ 7.85˜7.77 (m, 7H, Ar—H), δ7.32˜6.75 (m, 21H, Ar—H), δ 1.81˜1.43 (m, 18H, CH₂—H), δ 1.21˜1.15 (d,18H, CH₃—H)

Synthesis Example 4 Synthesis of Compound 726

Compound 726 was synthesized according to Reaction Scheme 22 below:

11.8 g of Compound 726 was obtained (yield: 46.5%) in the same manner asin the Synthesis of Compound 38, except that Intermediate 2-h was usedinstead of 1-bromopyrene and Intermediate 1-e was used instead ofIntermediate 1-g. Molecular weight: 1303.8

Elementary analysis: Calculated C, 88.44; H, 7.27; N, 4.30. Found C,88.43; H, 7.27; N, 4.30

1H NMR (CDCl₃): δ 8.22 (s, 2H, Ar—H), δ 7.82˜7.76 (m, 8H, Ar—H), δ7.45˜6.7 (m, 28H, Ar—H), δ 1.59˜1.31 (m, 32H, CH₂—H), δ 1.31˜1.15 (d,24H, CH₃—H)

Synthesis Example 5 Synthesis of Compound 929 Synthesis of Intermediate5-a

Intermediate 5-a was synthesized according to Reaction Scheme 23 below:

42 g of Intermediate 5-a was obtained (yield: 51.5%) in the same manneras in the Synthesis of Intermediate 1-a, except that3-methylphenylhydrazine was used instead of phenylhydrazine.

Synthesis of Intermediate 5-b

Intermediate 5-b was synthesized according to Reaction Scheme 24 below:

28.3 g of Intermediate 5-b was obtained (yield: 58.2%) in the samemanner as in the Synthesis of Intermediate 1-b, except that Intermediate5-a was used instead of Intermediate 1-a.

Synthesis of Intermediate 5-c

Intermediate 5-c was synthesized according to Reaction Scheme 25 below:

28.3 g (0.131 mol) of Intermediate 5-b and 85 ml of dimethylformamidewere put into a 500 ml round-bottom flask, and the temperature wasdecreased to 0° C. Then, 23.4 g (0.131 mol) of N-bromosuccinimide wasdissolved in 142 ml of dimethylformamide and the solution was slowlyadded to the mixture, and the temperature was raised to room temperatureand the resultant solution was stirred for 2 hours. After the reactionwas completed, the resultant solution was extracted with water anddichloromethane to separate the organic layer. The obtained organiclayer was dried with anhydrous magnesium sulfate and concentrated underreduced pressure. Thereafter, the resulting product was purified bycolumn chromatography using hexane and ethyl acetate as eluent. As aresult, 29.8 g of Intermediate 5-c was obtained (yield: 77%).

Synthesis of Intermediate 5-d

Intermediate 5-d was synthesized according to Reaction Scheme 26 below:

25.9 g of Intermediate 5-d was obtained (yield: 69%) in the same manneras in the Synthesis of Intermediate 1-c, except that Intermediate 5-cwas used instead of Intermediate 1-b.

Synthesis of Intermediate 5-e

Intermediate 5-e was synthesized according to Reaction Scheme 27 below:

13.4 g of Intermediate 5-e was obtained (yield: 45.9%) in the samemanner as in the Synthesis of Intermediate 1-e, except that Intermediate5-d was used instead of Intermediate 1-d.

Synthesis of Compound 929

Compound 929 was synthesized according to Reaction Scheme 28 below:

5.1 g of Compound 929 was obtained (yield: 34.5%) in the same manner asin the Synthesis of Compound 38, except that 9,10-dibromoanthracene wasused instead of 1-bromopyrene and Intermediate 5-e was used instead ofIntermediate 1-g. Molecular weight: 757.06

Elementary analysis: Calculated C, 88.84; H, 7.46; N, 3.70. Found C,88.79; H, 7.65; N, 3.56

1H NMR (CDCl₃): δ 7.85˜7.79 (m, 4H, Ar—H), δ 7.43˜6.81 (m, 18H, Ar—H), δ2.64 (s, 6H, CH₃—H), δ 1.61˜1.33 (m, 16H, CH₂—H), δ 1.31˜1.15 (d, 12H,CH₃—H)

Evaluation Example 1 Thermo Gravimetric Analysis (TGA)

The results of thermal analysis performed on each of Compounds 38, 262,586, 726, and 929 using TGA and differential scanning calorimetry (DSC)(N₂ atmosphere, range of temperature: room temperature to 600° C. (10°C./min)-TGA, room temperature to 400° C. (10° C./min)-DSC, and Pan Type:Pt Pan in disposable Al pan (TGA), disposable Al pan (DSC)) areillustrated in FIGS. 2 through 6. From the results shown in FIGS. 2through 6, it is confirmed that Compounds 38, 262, 586, 726, and 929have good thermal stability.

Example 1

An ITO glass substrate was patterned to have an emission area of 2 mm×2mm and then washed. The ITO glass was placed in a vacuum chamber,CuPc(800 Å) and α-NPD(300 Å) were sequentially formed on the ITO glassat a base pressure of 1×10⁻⁷ torr to form an HIL and an HTL,respectively. BH1 as a host and Compound 38 as a dopant wereco-deposited on the HTL at a ratio of 97:3 to form an EML having athickness of 250 Å. Alq3(350 Å), LiF (5 Å) and Al (500 Å) weresequentially deposited on the EML, and thereby an OLED sequentiallyincluding an ETL, an EIL, and a cathode was manufactured.

Example 2

An OLED was manufactured in the same manner as in Example 1, except thatCompound 262 was used instead of Compound 38 during EML formation.

Example 3

An OLED was manufactured in the same manner as in Example 1, except thatCompound 586 was used instead of Compound 38 during EML formation.

Example 4

An OLED was manufactured in the same manner as in Example 1, except thatCompound 726 was used instead of Compound 38 during EML formation.

Example 5

An OLED was manufactured in the same manner as in Example 1, except thatCompound 929 was used instead of Compound 38 during EML formation.

Comparative Example 1

An OLED was manufactured in the same manner as in Example 1, except thatCompound A below was used instead of Compound 38 during EML formation.

Comparative Example 2

An OLED was manufactured in the same manner as in Example 1, except thatCompound B below was used instead of Compound 38 during EML formation.

Comparative Example 3

An OLED was manufactured in the same manner as in Example 1, except thatCompound C below was used instead of Compound 38 during EML formation.

Evaluation Example 2

The driving voltage, current, luminance (measured at 0.4 mA), colorcoordinates, and lifetime (T97) of each of the OLEDs manufacturedaccording to Examples 1 through 5 and Comparative Examples 1 through 3were measured using a PR650 Spectroscan Source Measurement Unit(manufactured by PhotoResearch), and the measurement results are shownin Table 1 below. A voltage-current density graph is illustrated in FIG.7, a voltage-efficiency graph is illustrated in FIG. 8, and aphotoluminescence (PL) spectrum is illustrated in FIG. 9. T97 indicatesthe time at which the luminance of each of the OLEDs decreased to 97% ofthe initial luminance and it was measured at 3,000 nit.

TABLE 1 Current Lum. density eff. Lum. EML Vol. (mA/ (cd/ (cd/ T97dopant (V) cm²) A) m²) CIEx CIEy (hr) Ex. 1 Com- 3.7 10 8.8 883 0.1360.123 308 pound 38 Ex. 2 Com- 4.0 10 7.1 713 0.138 0.110 250 pound 262Ex. 3 Com- 4.0 10 6.2 618 0.141 0.125 150 pound 586 Ex. 4 Com- 3.9 107.9 793 0.142 0.118 500 pound 726 Ex. 5 Com- 3.8 0 0.5 851 0.143 0.114150 pound 929 Comp. Com- 4.3 0 0.06 534 0.133 0.137 45 Ex. 1 pound AComp. Com- 5.1 0 0.59 504 0.134 0.144 35 Ex. 1 pound B Comp. Com- 4.3 00.81 380 0.151 0.178 10 Ex. 2 pound C

From the results shown in Table 1, it is confirmed that the OLEDs ofExamples 1 through 5 each have good driving voltage, higher luminanceefficiency, higher luminance, higher color purity, and longer lifetimes,as compared to the OLEDs of Comparative Examples 1 through 3.

As described above, the OLEDs including the condensed-cyclic compoundmay have low driving voltages, high luminance, high efficiency, and longlifetimes.

While the present invention has been illustrated and described withreference to exemplary embodiments thereof, it will be understood bythose of ordinary skill in the art that various changes to the describedembodiments may be made without departing from the spirit and scope ofthe present invention as defined by the following claims.

What is claimed is:
 1. A condensed-cyclic compound represented byFormula 1:Ar₁

Ar₂)_(q)  Formula 1 wherein: q is an integer of 1 to 6, and when q is 2or greater, 2 or more of Ar₂ are identical to or different from eachother; Ar₂ is represented by Formula 2:

 wherein Cy is a substituted or unsubstituted C₃ to C₈ cycloalkane; X₁is N(R₁₁), B(R₁₁), Si(R₁₁)(R₁₂), O, or S; X₂ is a single bond or—[C(R₁₅)(R₁₆)]_(n)—, wherein n is an integer of 1 to 3, and when n is 2or greater, 2 or more R₁₅ and R₁₆ groups are identical to or differentfrom each other; L₁ is a single bond, a substituted or unsubstitutedC₁-C₆₀ alkylene group, a substituted or unsubstituted C₂-C₆₀ alkynylenegroup, a substituted or unsubstituted C₃-C₆₀ cycloalkylene group, asubstituted or unsubstituted C₂-C₆₀ heterocycloalkylene group, asubstituted or unsubstituted C₅-C₆₀ arylene group, or a substituted orunsubstituted C₂-C₆₀ heteroarylene; R₁ through R₃, R₁₁, R₁₂, R₁₅, andR₁₆ are each independently hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxylic acid group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₁-C₆₀ alkylthiogroup, a substituted or unsubstituted C₃-C₆₀ cycloalkyl group, asubstituted or unsubstituted C₅-C₆₀ aryl group, a substituted orunsubstituted C₅-C₆₀ aryloxy group, a substituted or unsubstitutedC₅-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a (substituted or unsubstituted C₁-C₆₀ alkyl) amino group, adi(substituted or unsubstituted C₁-C₆₀ alkyl) amino group, or a(substituted or unsubstituted C₅-C₆₀ aryl) amino group, a di(substitutedor unsubstituted C₅-C₆₀ aryl) amino group; a is an integer of 1 to 3,and when a is 2 or greater, 2 or more R₃ groups are identical to ordifferent from each other; and * is a binding site to Ar₁ of Formula 1;and Ar₁ is represented by any one of Formulae 3A through 3C and 3E-3G:

wherein R₂₀ through R₃₉ are each independently a binding site to Ar₂represented by Formula 2, hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxylic acid group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₁-C₆₀ alkylthiogroup, a substituted or unsubstituted C₃-C₆₀ cycloalkyl group, asubstituted or unsubstituted C₅-C₆₀ aryl group, a substituted orunsubstituted C₅-C₆₀ aryloxy group, a substituted or unsubstitutedC₅-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a(substituted or unsubstituted C₁-C₆₀ alkyl) amino group, adi(substituted or unsubstituted C₁-C₆₀ alkyl) amino group, or a(substituted or unsubstituted C₅-C₆₀ aryl) amino group or adi(substituted or unsubstituted C₅-C₆₀ aryl) amino group, wherein one tosix groups selected from R₂₀ through R₃₉ are binding sites to Ar₂represented by Formula
 2. 2. The condensed-cyclic compound of claim 1,wherein Ar₁ is represented by any one of Formulae 3A-1 through 3C-1 and3E-1 through 3G-1:

wherein R₂₀ through R₂₅ are each independently any one of a binding siteto Ar₂ represented by Formula 2; hydrogen; deuterium; a halogen atom; ahydroxyl group; a cyano group; a nitro group; an amino group; an amidinogroup; hydrazine; hydrazone; a carboxylic acid group or a salt thereof;a sulfonic acid group or a salt thereof; a phosphoric acid group or asalt thereof; a C₁-C₁₀ alkyl group; a C₁-C₁₀alkoxy group; a C₁-C₁₀alkylthio group; a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and C₁-C₁₀alkylthio group substituted with one or more of deuterium, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, hydrazine, hydrazone, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof; a phenyl group; a naphthyl group; a fluorenylgroup; a phenanthrenyl group; an anthryl group; a pyrenyl group; achrysenyl group; a phenyl group, a naphthyl group, a fluorenyl group, aphenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenylgroup substituted with one or more of deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxylic acid group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀alkylthio group; an indolyl group; a benzoimidazolyl group; a carbazolylgroup; an imidazolyl group; an imidazolynyl group; an imidazopyridinylgroup; an imidazopyrimidinyl group; a pyridinyl group; a pyrimidinylgroup; a triazinyl group; a quinolinyl group; an indolyl group, abenzoimidazolyl group, a carbazolyl group, an imidazolyl group, animidazolynyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and aquinolinyl group substituted with one or more of deuterium, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, hydrazine, hydrazone, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aC₁-C₁₀ alkylthio group, a phenyl group, and a naphthyl group; adi(C₁-C₁₀ alkyl) amino group; and a di(C₆-C₂₀ aryl) amino group, whereinthe C₆-C₂₀ aryl group is a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthryl group, a pyrenyl group, or achrysenyl group; at least one of R₂₀ through R₂₃ of Formulae 3A-1 and3C-1 is a binding site to Ar₂ represented by Formula 2; at least one ofR₂₄ through R₂₅ of Formula 3A-2 is a binding site to Ar₂ represented byFormula 2; at least one of R₂₀ through R₂₁ of Formulae 3B-1, 3E-1, 3F-1,and 3G-1 is a binding site to Ar₂ represented by Formula 2; and at leastone of R₂₂ through R₂₃ of Formulae 3B-2, 3E-2, and 3F-2 is a bindingsite to Ar₂ represented by Formula
 2. 3. The condensed-cyclic compoundof claim 1, wherein Ar₁ is represented by any one of Formulae 3A-1through 3B-1 below:

wherein R₂₀ through R₂₃ are each independently a binding site to Ar₂represented by Formula 2; hydrogen; deuterium; a halogen atom; ahydroxyl group; a cyano group; a nitro group; an amino group; an amidinogroup; hydrazine; hydrazone; a carboxyl group or a salt thereof; asulfonic acid group or a salt thereof; a phosphoric acid or a saltthereof; a C₁-C₁₀ alkyl group; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthiogroup; a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀alkylthio group substituted with one or more of deuterium, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, and a phosphoric acid or a saltthereof; a phenyl group; a naphthyl group; a fluorenyl group; aphenanthrenyl group; an anthryl group; a pyrenyl group; a chrysenylgroup; a phenyl group, a naphthyl group, a fluorenyl group, aphenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenylgroup substituted with one or more of deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀alkylthio group; a di(C₁-C₁₀ alkyl) amino group; and a di(C₆-C₂₀ aryl)amino group, wherein the C₆-C₂₀ aryl group is a phenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthryl group, apyrenyl group, or a chrysenyl group; at least one of R₂₀ through R₂₃ ofFormula 3A-1 is a binding site to Ar₂ represented by Formula 2; and atleast one of R₂₀ and R₂₁ of Formula 3B-1 is a binding site to Ar₂represented by Formula
 2. 4. The condensed-cyclic compound of claim 1,wherein X₁ in Formula 2 is N(R₁₁), B(R₁₁), or Si(R₁₁)(R₁₂), wherein R₁₁and R₁₂ are each independently hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxylic acid group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₂-C₂₀ alkenyl group, a substituted orunsubstituted C₂-C₂₀ alkynyl group, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted pentalenyl, a substitutedor unsubstituted indenyl, a substituted or unsubstituted naphthyl group,a substituted or unsubstituted azulenyl, a substituted or unsubstitutedheptalenyl, a substituted or unsubstituted indacenyl, a substituted orunsubstituted acenaphthyl group, a substituted or unsubstitutedfluorenyl group, a substituted or unsubstituted phenalenyl group, asubstituted or unsubstituted phenanthrenyl group, a substituted orunsubstituted anthryl group, a substituted or unsubstitutedfluoranthenyl group, a substituted or unsubstituted triphenylenyl group,a substituted or unsubstituted pyrenyl group, a substituted orunsubstituted chrysenyl group, a substituted or unsubstitutednaphthacenyl group, a substituted or unsubstituted picenyl group, asubstituted or unsubstituted perylenyl group, a substituted orunsubstituted pentaphenyl group, a substituted or unsubstitutedhexacenyl group, a substituted or unsubstituted pyrrolyl group, asubstituted or unsubstituted pyrazolyl group, a substituted orunsubstituted imidazolyl group, a substituted or unsubstitutedimidazolinyl group, a substituted or unsubstituted imidazopyridinylgroup, a substituted or unsubstituted imidazopyrimidinyl group, asubstituted or unsubstituted pyridinyl group, a substituted orunsubstituted pyrazinyl group, a substituted or unsubstitutedpyrimidinyl group, a substituted or unsubstituted indolyl group, asubstituted or unsubstituted purinyl group, a substituted orunsubstituted quinolinyl group, a substituted or unsubstitutedphthalazinyl group, a substituted or unsubstituted indolizinyl group, asubstituted or unsubstituted naphthyridinyl group, a substituted orunsubstituted quinazolinyl group, a substituted or unsubstitutedcinnolinyl group, a substituted or unsubstituted indazolyl group, asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted phenazinyl group, a substituted or unsubstitutedphenanthridinyl group, a substituted or unsubstituted pyranyl group, asubstituted or unsubstituted chromenyl group, a substituted orunsubstituted furanyl group, a substituted or unsubstituted benzofuranylgroup, a substituted or unsubstituted thiophenyl group, a substituted orunsubstituted benzothiophenyl group, a substituted or unsubstitutedisothiazolyl group, a substituted or unsubstituted benzoimidazolylgroup, a substituted or unsubstituted isoxazolyl group, a substituted orunsubstituted dibenzothiophenyl group, a substituted or unsubstituteddibenzofuranyl group, a substituted or unsubstituted triazinyl group, ora substituted or unsubstituted oxadiazolyl group.
 5. Thecondensed-cyclic compound of claim 1, wherein X₁ in Formula 2 is N(R₁₁),B(R₁₁), or Si(R₁₁)(R₁₂), wherein R₁₁ and R₁₂ are each independentlyrepresented by any one of Formulae 4A through 4H:

wherein Z₁ through Z₇ are each independently any one of hydrogen;deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitrogroup; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkylgroup; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group substitutedwith one or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, and a phosphoric acid group or a salt thereof;a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenylgroup; an anthryl group; a pyrenyl group; a chrysenyl group; a phenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthryl group, a pyrenyl group, and a chrysenyl group substituted withone or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group;an indolyl group; a benzoimidazolyl group; a carbazolyl group; animidazolyl group; an imidazolynyl group; an imidazopyridinyl group; animidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; atriazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolylgroup, a carbazolyl group, an imidazolyl group, an imidazolynyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, and a quinolinyl groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthiogroup, a phenyl group, and a naphthyl group; a di(C₁-C₁₀ alkyl) aminogroup; and a di(C₆-C₂₀ aryl) amino group, wherein the C₆-C₂₀ aryl groupis a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthryl group, a pyrenyl group, or a chrysenyl group.
 6. Thecondensed-cyclic compound of claim 1, wherein X₁ in Formula 2 is O or S.7. The condensed-cyclic compound of claim 1, wherein X₂ in Formula 2 isa single bond.
 8. The condensed-cyclic compound of claim 1, wherein L₁in Formula 2 is a single bond, a substituted or unsubstituted phenylenegroup, a substituted or unsubstituted pentalenylene group, a substitutedor unsubstituted indenylene group, a substituted or unsubstitutednaphthylene group, a substituted or unsubstituted azulenylene group, asubstituted or unsubstituted heptalenylene group, a substituted orunsubstituted indacenylene group, a substituted or unsubstitutedacenaphthylene group, a substituted or unsubstituted fluorenylene group,a substituted or unsubstituted phenalenylene group, a substituted orunsubstituted phenanthrenylene group, a substituted or unsubstitutedanthrylene group, a substituted or unsubstituted fluoranthenylene group,a substituted or unsubstituted triphenylenylene group, a substituted orunsubstituted pyrenylene group, a substituted or unsubstitutedchrysenylene group, a substituted or unsubstituted naphthacenylenegroup, a substituted or unsubstituted pycenylene group, a substituted orunsubstituted perylenylene group, a substituted or unsubstitutedpentacenylene group, a substituted or unsubstituted hexacenylene group,a substituted or unsubstituted pyrrolylene group, a substituted orunsubstituted pyrazolylene group, a substituted or unsubstitutedimidazolylene group, a substituted or unsubstituted imidazolinylenegroup, a substituted or unsubstituted imidazopyridinylene group, asubstituted or unsubstituted imidazopyrimidinylene group, a substitutedor unsubstituted pyridinylene group, a substituted or unsubstitutedpyrazinylene group, a substituted or unsubstituted pyrimidinylene group,a substituted or unsubstituted indolylene group, a substituted orunsubstituted purinyl group, a substituted or unsubstituted quinolinylgroup, a substituted or unsubstituted phthalazinyl group, a substitutedor unsubstituted indolizinylene group, a substituted or unsubstitutednaphthyridinylene group, a substituted or unsubstituted quinazolinylenegroup, a substituted or unsubstituted cinnolinylene group, a substitutedor unsubstituted indazolylene group, a substituted or unsubstitutedcarbazolylene group, a substituted or unsubstituted phenazinylene group,a substituted or unsubstituted phenanthridinylene group, a substitutedor unsubstituted pyranylene group, a substituted or unsubstitutedchromenylene group, a substituted or unsubstituted furanylene group, asubstituted or unsubstituted benzofuranylene group, a substituted orunsubstituted thiophenylene group, a substituted or unsubstitutedbenzothiophenylene group, a substituted or unsubstituted isothiazolylenegroup, a substituted or unsubstituted benzoimidazolylene group, asubstituted or unsubstituted isoxazolylene group, a substituted orunsubstituted dibenzothiophenylene group, a substituted or unsubstituteddibenzofuranylene group, a substituted or unsubstituted triazinylenegroup, or a substituted or unsubstituted oxadiazolylene group.
 9. Thecondensed-cyclic compound of claim 1, wherein L₁ in Formula 2 is asingle bond or any one of Formulae 5A through 5K:

wherein Z₁₁ through Z₁₆ are each independently one of hydrogen;deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitrogroup; an amino group; an amidino group; hydrazine; hydrazone; acarboxylic acid group or a salt thereof; a sulfonic acid group or a saltthereof; a phosphoric acid group or a salt thereof; a C₁-C₁₀ alkylgroup; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group substitutedwith one or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, and a phosphoric acid group or a salt thereof;a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenylgroup; an anthryl group; a pyrenyl group; a chrysenyl group; a phenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthryl group, a pyrenyl group, and a chrysenyl group substituted withone or more of deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group;an indolyl group; a benzoimidazolyl group; a carbazolyl group; animidazolyl group; an imidazolinyl group; an imidazopyridinyl group; animidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; atriazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolylgroup, a carbazolyl group, an imidazolyl group, an imidazolinyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, and a quinolinyl groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthiogroup, a phenyl group, and a naphthyl group; a di(C₁-C₁₀ alkyl) aminogroup; and a di(C₆-C₂₀ aryl) amino group, wherein the C₆-C₂₀ aryl groupis a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthryl group, a pyrenyl group, or a chrysenyl group.
 10. Thecondensed-cyclic compound of claim 1, wherein Ar₂ is represented by anyone of Formulae 2A through 2K:

wherein X₁, L₁, R₁ through R₃, a, and * are as described in claim 1; R₄₀through R₅₁ are each independently one of hydrogen; deuterium; a halogenatom; a hydroxyl group; a cyano group; a nitro group; an amino group; anamidino group; hydrazine; hydrazone; a carboxylic acid group or a saltthereof; a sulfonic acid group or a salt thereof; a phosphoric acidgroup or a salt thereof; a C₁-C₁₀ alkyl group; a C₁-C₁₀ alkoxy group; aC₁-C₁₀ alkylthio group; a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, anda C₁-C₁₀ alkylthio group substituted by one or more of deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxylic acid groupor a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; a phenyl group; a naphthylgroup; a fluorenyl group; a phenanthrenyl group; an anthryl group; apyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenylgroup, and a chrysenyl group substituted with one or more of deuterium,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxylic acid groupor a salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, and a C₁-C₁₀ alkylthio group; an indolyl group; a benzoimidazolylgroup; a carbazolyl group; an imidazolyl group; an imidazolinyl group;an imidazopyridinyl group; an imidazopyrimidinyl group; a pyridinylgroup; a pyrimidinyl group; a triazinyl group; a quinolinyl group; anindolyl group, a benzoimidazolyl group, a carbazolyl group, animidazolyl group, an imidazolinyl group, an imidazopyridinyl group, animidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group, and a quinolinyl group substituted with one or more ofdeuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthio group, a phenyl group,and a naphthyl group; a di(C₁-C₁₀ alkyl) amino group; and a di(C₆-C₂₀aryl) amino group, wherein the C₆-C₂₀ aryl group is a phenyl group, anaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthrylgroup, a pyrenyl group, or a chrysenyl group.
 11. The condensed-cycliccompound of claim 10, wherein R₄₀ through R₅₁ are each independently anyone of hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyanogroup; a nitro group; an amino group; an amidino group; hydrazine;hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acidgroup or a salt thereof; a phosphoric acid group or a salt thereof; aC₁-C₁₀ alkyl group; a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkylthio group; anda C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthiogroup substituted with one or more of deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxylic acid group or a salt thereof,a sulfonic acid group or a salt thereof, and a phosphoric acid group ora salt thereof.
 12. The condensed-cyclic compound of claim 10, whereinR₁ through R₃ are each independently any one of hydrogen; deuterium; ahalogen atom; a hydroxyl group; a cyano group; a nitro group; an aminogroup; an amidino group; hydrazine; hydrazone; a carboxylic acid groupor a salt thereof; a sulfonic acid group or a salt thereof; a phosphoricacid group or a salt thereof; a C₁-C₁₀ alkyl group; a C₁-C₁₀ alkoxygroup; a C₁-C₁₀ alkylthio group; and a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, and a C₁-C₁₀ alkylthio group substituted with one or moreof deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, and a phosphoric acid group or a salt thereof.
 13. Thecondensed-cyclic compound of claim 1, wherein Ar₂ is represented byFormula 2-1:

wherein L₁, R₁ through R₃, a, and Cy are as described in claim 1; Z₁through Z₅ are each independently any one of hydrogen; deuterium; ahalogen atom; a hydroxyl group; a cyano group; a nitro group; an aminogroup; an amidino group; hydrazine; hydrazone; a carboxylic acid groupor a salt thereof; a sulfonic acid group or a salt thereof; a phosphoricacid group or a salt thereof; a C₁-C₁₀ alkyl group; a C₁-C₁₀ alkoxygroup; a C₁ -C₁₀ alkylthio group; a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, and a C₁-C₁₀ alkylthio group substituted with one or more ofdeuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, and a phosphoric acid group or a salt thereof; a phenyl group;a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthrylgroup; a pyrenyl group; a chrysenyl group; a phenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthryl group, apyrenyl group, and a chrysenyl group substituted with one or more ofdeuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, and a C₁-C₁₀ alkylthio group; an indolylgroup; a benzoimidazolyl group; a carbazolyl group; an imidazolyl group;an imidazolinyl group; an imidazopyridinyl group; an imidazopyrimidinylgroup; a pyridinyl group; a pyrimidinyl group; a triazinyl group; aquinolinyl group; an indolyl group, a benzoimidazolyl group, acarbazolyl group, an imidazolyl group, an imidazolinyl group, animidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group,a pyrimidinyl group, a triazinyl group, and a quinolinyl groupsubstituted with one or more of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthiogroup, a phenyl group, and a naphthyl group; a di(C₁-C₁₀ alkyl) aminogroup; and a di(C₆-C₂₀ aryl) amino group, wherein the C₆-C₂₀ aryl groupis a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthryl group, a pyrenyl group, or a chrysenyl group.
 14. Thecondensed-cyclic compound of claim 1, wherein the condensed-cycliccompound is one of Compounds 38, 262, 586, 726, or 929:


15. An organic light-emitting diode comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode, wherein theorganic layer comprises the condensed-cyclic compound according toclaim
 1. 16. The organic light-emitting diode of claim 15, wherein theorganic layer comprises at least one of a hole injection layer, a holetransport layer, a functional layer having hole injection and holetransport abilities, an emission layer, an electron transport layer, andan electron injection layer.
 17. The organic light-emitting diode ofclaim 16, wherein the organic layer comprises an emission layercomprising the condensed-cyclic compound.
 18. The organic light-emittingdiode of claim 17, wherein the emission layer further comprises a hostand the condensed-cyclic compound in the emission layer acts as adopant.
 19. The organic light-emitting diode of claim 18, wherein thehost comprises an anthracene-based compound represented by Formula 60:

wherein Ar₁₁ and Ar₁₂ are each independently a substituted orunsubstituted C₅-C₆₀ arylene group; Ar₁₃ and Ar₁₄ are each independentlya substituted or unsubstituted C₁-C₁₀ alkyl group or a substituted orunsubstituted C₅-C₆₀ aryl group; and e and f are each independently aninteger of 0 to 5.